Methyl 2-Allyl-3-hydroxy-5-methoxybenzoate → 6-Methoxy-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

HRID 613998Notes

Reaction equation

HRID 613998 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([OH:12])[C:5]=1[CH2:13][CH:14]=[CH2:15]>[OH-].[K+]>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]2[O:12][CH:14]([CH3:15])[CH2:13][C:5]=12)=[O:16]

Participants

3

Reactant 1

HCID 54346125Methyl 2-Allyl-3-hydroxy-5-methoxybenzoate

Product 1

HCID 543897576-Methoxy-2-methyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl esterYield 45%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

2-allyl-3-hydroxy-5-methoxybenzoic acid methyl ester is heated under nitrogen atmosphere to 260° C. for about 3 hours. Upon cooling, the reaction mass is dissolved in a small amount of 20%KOH and the aqueous alkaline solution is then extracted with ethyl ether. The organic phase is evaporated and the crude residue affords the title compound in 45% yield. B.p./0.3 mmHg 136°-38° C.

Workup

  1. temperatureUpon cooling
  2. extractionthe aqueous alkaline solution is then extracted with ethyl ether
  3. customThe organic phase is evaporated

Sources & evidence

ORD record
ord-f14be845cb99441b8bfddcfed918892d
Source dataset
uspto-grants-1979_03
Patent number
US04143055

Reaction notes

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